1990
DOI: 10.1071/ch9900629
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DNA-Binding Compounds. III. Synthesis of a Peptide-Linked Binuclear Platinum(II)-Terpyridine Complex

Abstract: A procedure has been developed for linking two terpyridineplatinum(II), Pt(tpy), chromophores by an oligopeptide chain. It relies on the use of a new reagent, succinimido 3- (triphenylmethylthio)propanoate (2), to acylate the amino end groups of an α,ω-diaminoalkane peptide. Subsequent deprotection of the sulfhydryl groups and coupling with [ (tpy )PtlICl ]CI yields the binuclear complexes in good yields. This procedure allowed the synthesis of [ ( tpy )PtS(CH2)2 CO-Gly-Gly-Gly-NH(CH2)3NHCO-(CH2)2SPt(tpy)Cl2 (… Show more

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Cited by 4 publications
(2 citation statements)
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“…Reductive amination between N-Boc-δ-aminobutanal 5 16 and crude norheroin 4 using NaBH(OAc) 3 gave Boc-protected amine 6 in 65% yield from heroin hydrochloride 3 . Acidic deprotection of 6 yielded primary amine 7 , which was coupled without purification with trityl-protected thiol 8 17 to give trityl protected heroin hapten 9 in 70% yield from Boc-protected amine 6 . At this point, trityl protected morphine hapten 10 was synthesized in 63% yield from Boc-protected amine 6 by saponification of protected heroin hapten 9 .…”
Section: Resultsmentioning
confidence: 99%
“…Reductive amination between N-Boc-δ-aminobutanal 5 16 and crude norheroin 4 using NaBH(OAc) 3 gave Boc-protected amine 6 in 65% yield from heroin hydrochloride 3 . Acidic deprotection of 6 yielded primary amine 7 , which was coupled without purification with trityl-protected thiol 8 17 to give trityl protected heroin hapten 9 in 70% yield from Boc-protected amine 6 . At this point, trityl protected morphine hapten 10 was synthesized in 63% yield from Boc-protected amine 6 by saponification of protected heroin hapten 9 .…”
Section: Resultsmentioning
confidence: 99%
“…Mass spectrum: m / z 157 ({(M − CO 2 − 2H)/2} 2+ , 100%), 243 ({CPh 3 } + , 10%). This compound has been prepared previously by a somewhat different method …”
Section: Methodsmentioning
confidence: 99%